Prom Night
by delenasflame
Summary: Damon has been trying to get Elena to go out with him since the beginning of their junior year, but due to Damon's "bad boy" reputation, Elena refuses to date him. AH/AU *I know it sounds cliched but if you'd read and/or review, I'd greatly appreciate it.*


Elena Gilbert, Caroline Forbes, and Bonnie Bennett are crowded around Elena's locker on a Friday afternoon. They are talking about their senior prom which is being held over the weekend. The girls haven't picked out dresses to wear yet, but Caroline suggests that the trio goes shopping after school that day.

"It's our last hoorah before graduation!" Caroline exclaims. "We have to look perfect!"

The three best friends continued talking until the warning bell rang, and Bonnie and Caroline walked away to their respective classes after making a plan to meet up at the mall an hour after school let out. As Elena closed her locker door, she heard footsteps behind her. She turned around and rolled her eyes at the person in front of her. Damon Salvatore, the "bad boy" of Mystic Falls High. With his blue eyes, black hair, and leather jackets, Damon has managed to get together with half the female population in high school, while also getting himself into trouble.

"What do you want, Damon?" Elena asked him, but she already had an idea. Ever since the beginning of their junior year last year, Damon had been trying to pursue her. Although there was no denying the attraction that Elena felt toward Damon, she had denied him over and over again because of his reputation.

He answered her question with a question. "Will you go to prom with me?"

Elena pondered over the question, but she already knew her answer. It was the same answer that she gave him all the other times he'd asked her out. She said no.

Although he wasn't surprised by her response, a look of disappointment settled over his features. He expected her to say no, but he hoped that maybe this time, her answer would be different.

"What will it take for you to say yes to me?" Damon asked Elena. She doesn't get the chance to answer because the bell rang, signaling her tardiness. She rushed off to class, trying to get there before she got into trouble with her teacher, and after staring after the spot that Elena just vacated, Damon headed to his class too.

* * *

After a long day at school, Elena went home. Knowing that she had to meet Caroline and Bonnie at the mall in an hour, she decided to freshen up and change into something more comfortable. Once she was dressed in her favorite t-shirt and a pair of jeans, she headed back out to her car to go to the mall. When she arrived, Bonnie and Caroline were sitting at a table with three slices of pizza. Elena walked over and took a seat. She greeted her friends and started to eat her slice of pizza.

When the three girls finished their food, they took off to the dress shop. When they arrived, they started looking through all kinds of dresses in different styles and colors.

The girls fell into a comfortable silence while looking through the various dresses, but the silence was broken when Bonnie asked the girls who they were going to prom with. "I'm taking Jer." Jeremy Gilbert, Elena's little brother by a year, who had been in a relationship with Bonnie for two years.

"Klaus and Tyler both asked me," Caroline responded. Klaus Mikaelson was all charm, and Caroline had a massive crush on him; Tyler Lockwood, on the other hand, was Caroline's ex-boyfriend who dumped her for "Slutty Sofie" a few months back. "I decided to take Klaus to see if there's something there. What about you, Elena?"

"Damon Salvatore asked me," replied Elena. Caroline and Bonnie immediately had smiles on their faces. They knew about Damon's persistent tendencies from what Elena told them, but they thought it was cute how the high school "bad boy" wanted to go out with their friend. "I told him no."

"You know, Elena, you can't say no to him forever," Caroline said.

"I know, but I'm hoping that one day he'll just stop asking me." Caroline rolled her eyes at Elena's oblivion. She knew that Damon's feelings weren't going anywhere. Stefan Salvatore, also known as the "good brother" was Damon's younger brother who was close friends with Caroline. He was also the reason why Caroline knew so much about Damon and his feelings for Elena. "And besides, Matt and I are going together."

Matt Donovan was one of Elena's oldest friends. The pair grew up together, and Elena had loved him with all her heart… as a friend. Matt felt more than that though. Elena agreed to go out with Matt in freshman year because she felt like she owed it to Matt and herself to see if they could be more that friends. They eventually broke up during sophomore year because Elena realized that it was lacking the passion that a successful relationship should have. They decided to stay friends though, and now they are closer than ever.

"Anyways, I think I found a few dresses that I'm going to try on. Are you girls ready?" That was Elena, trying to change the subject. Bonnie and Caroline went along with it, and they all walked to the fitting rooms.

Bonnie and Caroline found perfect dresses rather quickly; Bonnie's being a navy blue, strapless, floor length gown with a sweetheart neckline and a ruffled tiered skirt, and Caroline's being a mermaid-style, ivory gown that reached the floor with a strapless bodice and hourglass shape webbed in pearls and embellishments. At the knees, it flared out in a different, beautiful fabric.

Elena was a different story. She went through three dresses until she finally found the one she was wanted. It was perfect to her. When she walked out of her changing room for the fourth time that day, she was wearing a silk, pink-patterned dress that was floor length and strapless with a wrapped bodice, an A-line skirt with a fluted hem, and a bow where the zip was concealed in the back. The color of the dress matched the pink streak in her long, brown hair perfectly, and upon seeing herself in the mirror, she immediately fell in love with the dress. When she turned to Caroline and Bonnie for their thoughts, they nodded their heads in approval. This was the dress she was going to get.

After changing back into their normal clothes, the girls took the dresses to the front of the shop and paid. They walked into the food court, and had an early dinner, after which they said their goodbyes.

While walking to her car, Elena started thinking about how everyone says that high school is meant to be the best four years of your life. She didn't think that was true for her because in high school, she had both lost her parents in a car accident and ended a relationship with the first guy to ever love her like she deserved.

But on the drive home, Elena couldn't help but think about what one certain blue eyed boy would say when he saw her at prom the next night.

_Will he like my dress? What will he think when he sees me? What if I look ugly?_

Lost in her thoughts, she hadn't noticed that she had arrived home. It was almost 8 when she walked into her house. She started doing her homework for the weekend before calling it a night two hours later and going to bed.

* * *

At 9 o'clock at night, Damon got into his car. His destination was the gym. After school today, he finished up everything he needed to do to get ready for prom. Earlier in the day, he picked up his suit, everything was in order for him, but he was stressed out. He planned out everything with the idea that Elena would say "yes" to his request to accompany her to prom, but with rejection comes frustration. Hence the reason he was on the way to the gym.

When he arrived, he headed straight for the weight room. While he worked his muscles, he heard Matt Donovan, Jeremy Gilbert, Tyler Lockwood, and Klaus Mikaelson walk into the room. Tyler and Klaus were arguing over Caroline, while Matt and Jeremy were talking about the prom tomorrow night. Damon continued to work on his arms, but he didn't try to block out the sounds of the boys' voices.

"I've got the limo coming for the girls at 6:30 p.m. and the reservations at the restaurant are at 7," Jeremy told Matt. "I'll make sure my sister is ready."

_So that's why she rejected me,_ Damon told himself. _She's going with Donovan._

He kept working out as if the other boys weren't in the room, and after an hour, he hit the showers. While the water ran down his body, cleaning off the sweat from his work out, Damon started to think.

_What if Matt never asked her? Would she still say no to me? _Damon started feeling hopeful for a while before a nagging voice at the back of his head decided to speak up. _Of course she would. She doesn't like you. She doesn't want you._

Pushing his thoughts about Elena to the back of his head, he continued showering. Once he's done, he exited the gym, got into his car, and drove back home to get some much needed sleep.

* * *

Elena woke up on Saturday morning to the sound of her phone ringing. The name _Matt _flashed across the screen when she checked it. Sliding the green arrow across the screen, she held the phone up to her ear and said her greeting.

"Hi," she said.

"Elena, hey. Listen. I am so sorry for what I'm about to say, but I'm not going to be able to make it to prom. My mom just called. She told me that she's coming home tonight, and you know how it is. I need to take care of her," Matt explained to Elena. She knew better than to try and convince him to come, because the truth was, she did know what Matt's mom was like. When she was ever home, which is very rare, she got drunk out of her mind, and Matt, being the only remaining family she had left, felt responsible for taking care of her.

Sighing, Elena responded, "Matt, it's okay. But I don't need to go either. I can help you with your mom if you need me."

"No, Elena, you should go. This is senior prom! Remember what Care said? 'Our last hurrah before graduation!' But I promise, Lena. I'll make it up to you."

"Okay, I'll go. But don't hesitate for one second to call me if you need my help, okay?"

"Okay! Bye, Elena," Matt replied.

"Bye, Matt," Elena said before she ended the call. She then opened up a new text message to inform her friends about the change of plans.

_To: Caroline, Bonnie_

_**Matt's a no go for tonight. I'll tell you more later. 4:00 my place, right?**_

_**-Elena**_

After her friends confirmed the time, Elena hopped into the shower to prepare for her day. Standing under the warm spray, Elena went over the day's schedule in her head. First, she would go to lunch with Jeremy, Aunt Jenna, and Alaric, Jenna's boyfriend and Elena's history teacher. Then, she would come back home and look for accessories and shoes to match her outfit for prom. By the time she finishes that, Bonnie and Caroline should be over. The girls will get ready there, and then when they're done, they'd get into the limo with Jeremy and Klaus, and the group will head towards the restaurant where they will eat before heading off to the prom venue.

* * *

When Elena came home from lunch with her family, she went straight to her room. She told Jeremy about how Matt couldn't make it to the dance tonight while they were at lunch, and Bonnie and Caroline would be there in a few minutes. The sound of the doorbell ringing brought Elena out of her room for a few minutes. She made her way down the stairs, answered the door, and led her two best friends up to her room. The girls immediately started getting ready.

"Okay, Elena. Bonnie is doing my hair, and I'm doing both of yours. Can you do my makeup?" Caroline asked. Elena nodded.

"Cool. Let's get started," said Bonnie. And they did.

After Caroline had done Bonnie's and Elena's hair in waves, Elena started on Caroline's makeup while Bonnie did Caroline's hair.

"So why can't Matt go with you again?" Caroline asked.

"His mom is coming back into town today. You guys know how she is. He has to take care of her," Elena explained. "I offered to help him too, but he said that I should go tonight, so I am."

Caroline and Bonnie also knew about Matt's mom. She had a lot of problems, but having the town know her family's baggage was not one of them.

"Well if you don't have a date, then maybe… you could, I don't know… ask Damon if he'll go with you," at Bonnie's words, Elena glared in her friend's direction.

"I'm not going to go out with Damon. End of story," Elena clarified in a strict tone. Her friends dropped the subject as they continued getting ready, and when it was 6:30, the girls took one final look in the mirror.

Caroline's hair had a braid running from the side of her hair, along the nape of her neck, and into a bun with different flowery pins decorating it. Her makeup was light and matched her dress perfectly. She had on dangly earrings and a little necklace with a little jewel on it. Bonnie had her wavy hair bulled to the side, and her makeup complimented her dress perfectly. She wore a necklace and earrings, each with a dark blue stone to match her dress perfectly. Elena's wavy hair was in a half up, half down style to give her some volume. Her makeup was a little dark around the eyes and her lips were a shade of pink, but it suited her well. She had on dangly earrings but no other jewelry.

They were finally ready, and they looked perfect.

Making their way downstairs, Jenna insisted on taking pictures of them, so the girls smiled and went along with it. The limo arrived shortly after, and when the girls and boys were settled inside, they headed for the restaurant.

* * *

Elena felt like a fifth wheel all through dinner. Both of her best friends and their dates were in conversation with each other when the limo pulled up to the prom venue. Elena was the first person out of the limo. She waited for her friends to get out and walked behind them into the building.

"Let's dance!" Caroline suggested. Bonnie nodded and pulled Jeremy toward the dance floor by the arm. Caroline and Klaus followed suit, but she turned around after a few steps. "Aren't you coming, Elena?"

Elena shook her head. "Not right now, Care. I'm just going to get some punch," she said while pointing at the punch bowl. Caroline accepted her answer and turned around, dragging Klaus back to the dance floor.

Elena was pouring a drink when someone came to stand next to her. She hoped to God that it wasn't who she thought it was. She also hoped that she looked alright just in case it was said person. She turned her head towards the person standing beside her. Not surprised to see Damon standing there, she turned to walk away.

"Still in denial, princess?" Damon said to her.

"You're even more delusional than I thought," Elena responded.

"Where's your date?"

"He's not coming," Elena answered, looking down at the floor with a shy smile. "Now, if you'll excuse me…" She was already walking away when Damon spoke up.

"Well he's missing out on how beautiful you look."

Turning back around, Elena asked, "what do you want, Damon?"

"Did you ever consider that maybe I just want you?"

"How many times have you used that line?" Elena asked with a skeptical look on her face.

"How does that even matter right now?" Damon asked her, flabbergasted.

"Maybe I don't want to be just another one of your conquests," Elena responded, walking away.

Damon watched her walk away while thinking about her last statement.

* * *

The dance was coming to an end, and Elena was thankful that she'd be able to go home soon. Unfortunately, the next song was a slow one "for all the couples out there." Elena took a seat at one of the tables and watched as Klaus and Caroline walked toward the floor, hand in hand. Looking in a different direction, she spotted Jeremy and Bonnie swaying peacefully to the music.

Elena got up then and decided that if she left now, there was a possibility that her friends wouldn't even notice. She was almost to the door when Damon stepped in her path.

"What now, Damon?"

"I know what you said earlier, and I get that you don't particularly like me, but would you dance with me? Just this once?" He held his hand out to Elena hoping she'd accept.

"Oh, what the hell," Elena said, taking his outstretched hand.

_Yes, _Damon exclaimed, in his thoughts. He had to admit that he was majorly surprised that she agreed to dance.

She led the way to the dance floor, and when they stepped onto it, Elena turned and put her hands around his neck. Damon wrapped his arms around her waist to pull her closer to him, and they started to sway to the music. It was quiet between the two until Elena looked up and broke the silence.

"Damon…" Elena started.

Looking down at her, he nodded at her to continue speaking.

"Why are you so interested in me?" She was asking because she was genuinely curious.

"What do you mean?" he asked.

"_I mean_, for the past two years, you could've had any other girl in school – in town actually, but you chose me," she explained. "Why, though? What's so special about me?"

As he opened his mouth to answer, Caroline marched over to the duo.

"Elena! There you are! We thought you left!" Behind her, Klaus, Jeremy, and Bonnie were waiting.

"Nope, still here," said Elena, "but is this over? Can we leave now?"

After Caroline nodded, she turned around to lead the others out the door, Elena trailing behind the two couples. Before she could completely turn away though, Damon grabbed her arm.

"Will you meet me at The Grill in an hour?" Damon asked her.

"Why?"

"Don't you want the answer to your question?" He waited for her to confirm before repeating his question. "So you'll meet me in an hour?"

"Yeah, I'll see you there," she answered with a small smile on her face.

* * *

After prom, she went back to her house to change into something more comfortable, and now she was wearing her favorite skinny jeans, a white, oversized t-shirt, and some sandals. She had taken her hair down and braided it to the side to keep it out of the way. Then, she left her house again to meet Damon.

Elena was early to The Grill, so she decided to order a snack while she waited for him. She sat in a booth near the door so that she could watch out for him.

A while after the waiter placed a plate full of fries in front of her, Damon walked in. He, too, had changed. Now he was wearing a navy blue Henley and black pants. He walked toward the booth Elena was in when she waved him over. Sitting across from her, he popped a fry into his mouth.

"So, tell me," Elena said.

"You don't waste time, do you?" Damon joked. At Elena's playful glare, he started explaining his attraction to her. "Basically, you don't put up with bullshit. Other girls would do or say anything for my attention, not that I'm complaining. But you… you were different. It was like you didn't care." He took a break in his speaking to eat another fry.

"If you keep eating my food, you're going to have to pay," Elena said, playfully.

Damon smiled and responded, "I would've paid anyway."

"What a gentleman," Elena teased.

"Always," he replied with a smirk on his face before winking at her. Elena felt the blood rushing to her cheeks. "Elena Gilbert. Are you blushing?"

"No," she denied and looked down to try and conceal her face.

Damon reached across the table and put his hand under her chin to lift her head back up so that he could see her face. They stared at each other for a while, each with small smiles on their faces, before Damon decided to continue his story.

Pulling his hand back, Damon started speaking again. "Anyway, you were one of the few people who could actually resist my charm. And you know how they say that bad boys love the chase? It's true. I thought you were playing hard to get when I first tried to get you to go out with me, and that made me even more interested in you. However, when I realized that you _actually_ didn't want to date me, I wanted to have you more, so I never stopped trying. And the fact that you're pretty easy on the eyes didn't hurt either." And with that, Elena was blushing again.

* * *

Damon and Elena had been talking for a while, and Elena couldn't help but feel bad for all those times that she rejected him. Damon was great company with his witty remarks and corny jokes, and she was enjoying having him around. They were talking about their plans for the summer when Elena's phone rang. Giving Damon an apologetic look, she answered the phone.

"Hello?" She greeted.

"Elena, where are you?" Jenna asked from the other end.

"I told you that I was going to be at The Grill for a while," Elena answered.

"I know that, but I didn't think you were going to be out all night," said Jenna. "You should probably start coming home."

"Yeah, okay, I'll see you soon," she said, before saying bye and hanging up. She looked at Damon and started moving out of her side of the booth. "That was Jenna. I better get going."

"Yeah, me too. Stefan is probably wondering where I am. Did you drive here?" Damon asked.

"No, my house isn't that far of a walk."

"Let me drive you home," Damon offered after getting out of his seat, too. "It's dangerous at night." It wasn't really dangerous, because it was Mystic Falls and nothing bad ever happens there, but Damon wanted to make sure she got home safely.

"Sure. Thanks," Elena agreed. Damon led Elena out the door and toward his blue Chevy Camaro. He opened the passenger side door for Elena before moving around the front of the car to get to the driver's side. He started the car after getting settled in and drove out of the parking lot.

* * *

They arrived at Elena's house quickly, making small talk on the way there. Damon parked in front of Elena's house before getting out and opening her door. He walked behind her up to the door, and when they stopped in front of it, Elena turned to face Damon.

"Thank you for driving me home," said Elena, "and for walking me to my door."

"No problem," Damon replied with his usual smirk-smile. "I had fun tonight. Maybe we could do this again…" He trailed off unsure of what she would say.

"Sure. I'd like that. I had fun, too. You're not as bad as I thought you were."

"And you're even more fun than I thought you'd be. Thanks for coming tonight," Damon said, genuinely grateful that Elena showed up. After Elena nodded, they fell into an awkward silence.

"Well, I should probably get going. I'll see you later, Elena," Damon said, breaking the silence. He bent in to give her a kiss on the cheek, and Elena sucked in a gasp at the feel of his lips against her skin. Leaning back, Damon looked into her eyes before slowly leaning in again. She knew that this time he wouldn't be kissing her cheek, and to her own surprise, Elena found herself wanting to feel his lips against hers. Deciding that he was taking too long to meet her mouth, Elena wrapped her hand around his neck and brought his head down to hers. They stood, kissing, on Elena's front porch for a few minutes before Damon pulled away. His hands were on her hips, his eyes were still closed, and his lips were shaped into a satisfied smile. When he opened his eyes, he saw Elena's staring back at him with a shy smile on her face.

"Goodnight, Elena," he said, stepping back, letting go of Elena, and turning to walk back to his car.

"Wait, Damon! I have one more question." She waited until he was turned around to ask him. "Was it worth it?" He didn't expect tonight's kiss, but he got one after waiting two years for at least a date. She wanted to see if it was worth it, or if he'd wasted two years chasing after just another girl.

Walking backwards toward his car, he gave her an answer. "I'll tell you on our next date," he said with a smile.

Elena shook her head at him with a smile on her face and walked inside her house.

On the drive home, Damon pondered over Elena's question. _Was it worth it? _He decided that the question was one of the easiest he'd ever had to answer._ It was worth every second of the past two years. And I'd do it all over again._

* * *

**And they lived happily ever after…**

**The kiss is half inspired by the Damon and "Elena" kiss in 1x22 and half inspired by Delena in 3x10.**

**Thanks so much to Grace (elenasfire) for letting me use her AU Delena gifset (**_/_**post/48349246165)** **as inspiration. This is my first fanfiction and also the first time I'm posting on a website for others to read, so I really hope you guys liked it. Thanks for reading and please review if you liked it, and also if you have any pointers for me.**


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